Mediations #13: How to Delegate Successfully
The key to successful delegation is that leaders should delegate their strongest skills to people who are both capable and interested in learning them.
I had been struggling to find the right approach to delegation at work. I had made many small and big mistakes. Some have caused others frustration, and a few have cost time and financial loss. Now that I have gained experience, it’s time to share.
My most significant learning in delegation is this: a leader must delegate the work they know best or the skill they can perform well to the person who can and wants to acquire it.
It’s unintuitive. The strongest skills are often the reason someone is brought to a leadership position. Perhaps these skills helped solve a painful problem by doing a particular type of work well. Then why must they hand over that work or transfer the skill to others?
A new level was unlocked when I realized that mastering a skill and getting positive feedback constantly was a strong sign that it was time to transfer. Strong skills also make it easier to teach others how to do certain things, recognize when they need a hand, and ask the right questions when they don’t even know which questions are out there to answer.
For example, I’m a good meeting organizer when it comes to planning, standups, retrospectives, and even workshops; it is my strong suit. Moreover, I like doing these things. Organizing and facilitating these meetings well brings me joy and satisfaction as a group progresses through a successful process that results in alignment.
However, once I establish these processes, I look for people who can take over the facilitation. The facilitator’s role usually includes not only moderating the meetings but also doing pre-work, preparations and communication before and after the sessions. Moreover, the responsibilities also include following up on action items and other people’s work to ensure everyone follows the agreement. Last but not least, it also includes following the process itself and suggesting improvements and changes when the process doesn’t fit reality or starts to crack for various reasons.
Since I know all these expectations and how to navigate people around them, I can mentor or coach the person I’m delegating this work to.
Yet, many people (including myself) mistake delegation for a hands-off approach or delegate the wrong tasks to the wrong people. Let’s examine each one, starting with the last.
Finding the Right Person to Delegate
You shouldn’t delegate a task just because you want to do someone a favor. Understanding whom to delegate to demands skill mapping, career development, learning organizational constraints, careful staff planning, and proper decision-making.
If you’re leading a team, you must know your team members’ career plans, backgrounds, wishes, strengths, and weaknesses. Once you know who wants to go to the next level (maybe even your position) and which skills they lack, you can work with them members and train them.
Although all of these are necessary to choose, it doesn’t start with looking at people’s skills; it begins with—counterintuitively—you, the delegator.
You have to look at yourself first and answer the questions below openly, honestly, and transparently (for yourself).
What things take up a lot of your time and are trivial to do?
What are your strengths, and which initiatives use those strengths?
How much time would you spend when you delegate? How much time do you have available for the person?
What are the results do you expect?
If someone makes a bad decision, how bad can these decisions be?
These questions address the fundamental constraints: time, goals and risks.
People rarely consider their time when delegating, but it’s the most crucial element. Delegation is not about shifting a task and forgetting it (more on that below). As everyone is busy, you have to consider your time management and find the person with whom you can spend the right amount of time for the right thing.
If one team member demands an extra hour every day when you delegate, while another might be okay with 30 minutes a week, the answer may lie in your time. However, choosing a 30-minute one is not straightforward because you’ll need to invest in people equally, and each person’s constraints will be different.
Once you answer the questions, you must turn your attention to the people who you want to delegate. If you have more than one person, think about each of them one by one. Evaluate them by answering the following questions:
How much time would this person require from you?
What are the skills you have that helped you do the job so far and that the other person doesn’t have?
What are the common skills you both have that can help with the task?
How is this work aligned with the person’s career development?
Can this work be exciting for the person or draining their energy?
After answering these questions, you’ll know how much time you need to invest in the person and can plan your approach.
Understanding your needs and other people’s needs within your boundaries and constraints will help you avoid the most common mistake: defaulting to a hands-off approach.
Delegation doesn’t mean shift and forget
One of my mistakes after I delegated was not thinking about the work anymore. Even though I asked the person to reach out for help when they struggled, they rarely did. This is not because we didn’t trust each other or never communicated. Quite the contrary, I trusted them too much, and—I learned too late that—they tried to live up to that trust.
When people take on new work, they usually guess how to approach it. Based on an assumption, they try seemingly effective ways to make progress. Yet, they don’t notice that their methods are unsuitable. Because they have been trusted to do the work, they try whatever they can without asking for help. They think seeking help will make them look like they fail and can’t handle the delegated work. They think it’s their fault. However, we, the delegator, made a mistake, not them.
I see delegation as enhancing someone else’s tool belt. Everyone has skills (or rather tools in this metaphor) they know how to use. However, the world is full of tools they have no idea about. Delegation is like giving someone a tool as a gift and showing them how to use it well.
The first step of delegation is giving them clear directions and letting them try and fail within a safe zone. Once they fail and succeed a few times, they learn the basics. After some practice, they can do the job in the wild and develop their own style.
But how do we evaluate how much direction, safe-zoning, and freedom the person needs?
If someone is good at moderating the sprint planning, it doesn’t mean they will know how to moderate a retrospective meeting. Although both are team rituals, they are fundamentally different. So, handing over retrospective moderation will need some help to learn the basics. That requires understanding the task-relevant maturity of the person to whom you want to delegate the work.
Task-Maturity Scale
“How often you monitor should not be based on what you believe your subordinate can do in general, but on his experience with a specific task and his prior performance with it - his task-relevant maturity__…as the subordinate’s work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring.” — Andrew Groove, Co-founder & CEO of Intel
The main goal is to stretch the person’s skills by helping them, not burn them out. If we consider the new work on someone’s task-relevant maturity scale, it should fall into the delegation zone.
If the job is outside their comfort zone and too easy for them, it will be cumbersome and bore them out. Delegation should aim to place the skill beyond their comfort zone and before “beyond capability” because we want to mentor them first but teach a skill that needs development from the fundamentals. Beyond the delegation zone, the person is burdened instead of given help for growth.
Within the delegation zone, the person will still need different levels of help, ranging from strong mentoring to passive coaching. The caveat of the delegation zone is that it’s different for everyone. Hence, finding the right job and person match and giving them the right amount of help demands a careful approach.
Once you find the right person and have an idea about the amount of help they need, you can kick off strong.
Starting with the correct foot
At this stage, you have put in a lot of work, and it feels like you’re nearing the end. Many people rush this part, wasting all their effort.
You must set clear expectations and have a concrete conversation. The conversation has to be open, transparent, clear and genuine.
First, explain the context of the work. Provide all the background information, allow them to ask questions, and clearly answer all of them. It is crucial to explain the context, constraints, and current status.
Once they know the constraints and context, discuss your expectations and whether you need to adjust them. Expectations are always mutual. Listen to their expectations as well. Talk openly and agree together.
Define how the success looks like. If you’re delegating the leadership of a project, don’t say, “The project is completed on time and within budget.” Go beyond that and focus on how they will make it happen. If the project is a success in the end, but everyone is burned out along the way, can we call the project a big success? Clearly define what success means and help them figure out how to achieve it.
Write all of these down. Verbal communication often has cultural misunderstandings. However, once agreements are written, people come to a shared understanding. A few months later, you can look at what you’ve written and evaluate the progress clearly.
Set recurring check-ins. If you already have one-on-ones, reserve the last five minutes for them. Taking from the previous example, don’t talk about the project itself during these five minutes but more about the experience of leading it. Look back at what changed from the last check-in, how the person has improved, and whether there is anything they can do better, need extra support, or need changes in expectations.
Conclusion
When leaders devote too much time to their strong skills, they don’t learn at work, which increases their dissatisfaction. They also limit their impact; instead of focusing on the bigger picture, they get stuck on smaller initiatives. They fear delegation will take their jobs away or make them dormant.
Just because they don’t know how or what to delegate, they keep doing whatever they are good at. However, the other side of the road is a path to increasing impact and job satisfaction. Once learned, delegation unlocks many different opportunities.
Although I discussed what I learned from my mistakes, you’ll still have to make yours. Without mistakes, there is no learning. And don’t forget: Everyone has a right to fail, including me, you, and the person you delegate the task to.